Located near the southern tip of the South Loop, Acadia is only a five-minute drive from the heart of the Financial District and downtown. Owner Ryan McCaskey was an accomplished chef long before he set sights on opening this highly successful boutique-style eatery in an industrial part of town. Acadia specializes in seasonal New England fare, with a strong emphasis on Maine, McCaskey's stomping grounds. That means, of course, you'll find a nice share of seafood on the menu. There's an exceptional wine selection, well-curated craft beer list, and outstanding mocktail and cocktail program. Indulge in dinner in the main dining room or chill out with more casual bites and drinks in the adjacent lounge. If you're ordering one of the tasting menus, cross your fingers that you'll be lucky enough to get McCaskey's signature Maine lobster rolls — in miniature form. Diners may order a la carte, five- or 10-course tasting menus, or the Grand Tour tasting menu.

Open since 1939 in the same location, Blackie's South Loop has been family owned for four generations. Throughout the years, it's hosted its fair share of celebrity diners, including the likes of Tony Bennett, Dean Martin, Jerry Lewis, Frank Sinatra and Elizabeth Taylor. Of course, they have the photos on the wall to prove it. For those wanting to start off the day with a hot, home-style meal, Blackie's offers breakfast on weekends. Diners may choose from chocolate chip pancakes, steak and eggs, or a vegetarian soufflé omelet. Stopping by for lunch or dinner? The signature salmon burger served with house-made chipotle aioli or BBQ ribs come highly recommended.

Located on the historic property of the Renaissance Blackstone Chicago Hotel —which has played host to 12 U.S. presidents since opening in 1910 — Mercat a la Planxa serves modern Spanish fare. There's brunch through dinner featured, but the paella choices are where Mercat excels. They change seasonally with offerings such as smoked eggplant, rabbit or various seafood selections. Those coming for brunch may order dishes like brioche French toast topped with smoked honey butter, shrimp and grits or the Blackstone Benedict with toasted brioche, chorizo, truffled hollandaise and breakfast potato.

Those planning to cycle their way through the city should make a stopover at Spoke & Bird for a late lunch. The quaint little American cafe is very bike-centric with a bike corral and Divvy bike rack nearby. During warm months, there's a 110-seat patio for guests to dine and drink. Highlights of the menu range from sandwiches (BLT, grilled cheese, smoked turkey) to seasonal salads.

Authentic Spanish fare gets more love at Tapas Valencia, a neighborhood favorite that's affordable and also open for weekend brunch. The cheery venue is bright and welcoming to larger groups, and most dishes may be shared. In addition to paella, there's traditional Serrano ham, marinated Spanish olives, stuffed mushroom caps and empanadas filled with beef tenderloin. Those coming for Sunday brunch may indulge in filet mignon Benedict, a Spanish omelet of potato, chorizo and onion, or pancakes topped with a brown sugar-Torres orange liquor syrup.

Every imaginable waffle flavor is featured at this South Loop BYOB gem that draws long lines on weekends. Get ready to wait because Chicago Waffles has cornered the market on sweet and savory breakfast/brunch treats. On the savory side: bacon & chicken, cheddar and short rib, or the waffle "sandwich" of eggs, bacon or turkey bacon and American cheese. Those with a sweet tooth should appreciate best sellers like red velvet, cinnamon roll or chocolate. And those who cannot make up their minds may select the waffle "flight" of three of the sweet treats. There are also omelets, pancakes and burgers on the menu.

Little Branch Cafe, located near Chicago's museum campus, has been delighting Chicagoans with their brunch fare and Metropolis coffee for over a decade. Visit here, in the light-filled dining room, to nosh on a loaded bagel, panini, or a fresh salad. Kids will love the hot cocoa with whipped creme and the grilled cheese with fries. If you're short on time, order your food to-go and enjoy a picnic outdoors.

The award-winning Asian Outpost has been voted the best Pan-Asian comfort food in the city, which is really saying something because Chicago has many restaurants to choose from. The dishes here are inspired by food from Vietnam, Thailand, Korea, Japan, Indonesia, China and Hawaii. Visit for the sushi, noodles, soup and fried rice. Vegan and vegetarian diners will have many options—wraps, rolls, salads and bowls.

For an old school family diner experience, visit Eleven City Diner, a Jewish delicatessen. The owner, Bradley Rubin, grew up in Chicago but visited all 50 United States via motorbike, which gave him a unique insight into the American experience with food culture. Order a lox and latke, pastrami on rye and a slice of pie—you can't go wrong.